Carbonyl-Ene Approach to the Asymmetric Synthesis of 2-Keto-3-Deoxy-D-Gluconic Acid (KDG): A Combinatorial Sequence Using Sharpless Epoxidation

Synlett

Volumn 1996, Issue 11, 1996, Pages 1112-1114

  Shimizu, Masaki ^a   Yoshida, Akihiro ^a   Mikami, Koichi ^a  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

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Indexed keywords

EID: 1542499810     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1996-5691     Document Type: Article

References (35)

1. Reviews: (a) Mikami, K. Pure Appl. Chem. 1996, 68, 639-644. (b) Mikami, K. In Advances in Asymmetric Synthesis; Hassner, A., Ed.; JAI Press: Greenwich, Connecticut, 1995; Vol. 1, pp 1-44. (c) Mikami, K.; Terada, M.; Nakai, T. In Advances in Catalytic Processes; Doyle, M. P., Ed.; JAI Press: Greenwich, Connecticut, 1995; Vol. 1, pp 123-149. (d) Mikami, K.; Terada, M.; Narisawa, S.; Nakai , T. Synlett 1992, 255-265. (e) Mikami, K.; Shimizu, M. Chem. Rev. 1992, 92, 1021-1050. (f) Yamamoto, H.; Maruoka, K.; Furuta, K. In Selectivities in Lewis Acid Promoted Reactions; Schinzer, D., Ed; Kluwer Academic Publishers: London, 1989; pp 281-294.
2. Reviews: (a) Mikami, K. Pure Appl. Chem. 1996, 68, 639-644. (b) Mikami, K. In Advances in Asymmetric Synthesis; Hassner, A., Ed.; JAI Press: Greenwich, Connecticut, 1995; Vol. 1, pp 1-44. (c) Mikami, K.; Terada, M.; Nakai, T. In Advances in Catalytic Processes; Doyle, M. P., Ed.; JAI Press: Greenwich, Connecticut, 1995; Vol. 1, pp 123-149. (d) Mikami, K.; Terada, M.; Narisawa, S.; Nakai , T. Synlett 1992, 255-265. (e) Mikami, K.; Shimizu, M. Chem. Rev. 1992, 92, 1021-1050. (f) Yamamoto, H.; Maruoka, K.; Furuta, K. In Selectivities in Lewis Acid Promoted Reactions; Schinzer, D., Ed; Kluwer Academic Publishers: London, 1989; pp 281-294.
3. Reviews: (a) Mikami, K. Pure Appl. Chem. 1996, 68, 639-644. (b) Mikami, K. In Advances in Asymmetric Synthesis; Hassner, A., Ed.; JAI Press: Greenwich, Connecticut, 1995; Vol. 1, pp 1-44. (c) Mikami, K.; Terada, M.; Nakai, T. In Advances in Catalytic Processes; Doyle, M. P., Ed.; JAI Press: Greenwich, Connecticut, 1995; Vol. 1, pp 123-149. (d) Mikami, K.; Terada, M.; Narisawa, S.; Nakai , T. Synlett 1992, 255-265. (e) Mikami, K.; Shimizu, M. Chem. Rev. 1992, 92, 1021-1050. (f) Yamamoto, H.; Maruoka, K.; Furuta, K. In Selectivities in Lewis Acid Promoted Reactions; Schinzer, D., Ed; Kluwer Academic Publishers: London, 1989; pp 281-294.
4. Reviews: (a) Mikami, K. Pure Appl. Chem. 1996, 68, 639-644. (b) Mikami, K. In Advances in Asymmetric Synthesis; Hassner, A., Ed.; JAI Press: Greenwich, Connecticut, 1995; Vol. 1, pp 1-44. (c) Mikami, K.; Terada, M.; Nakai, T. In Advances in Catalytic Processes; Doyle, M. P., Ed.; JAI Press: Greenwich, Connecticut, 1995; Vol. 1, pp 123-149. (d) Mikami, K.; Terada, M.; Narisawa, S.; Nakai , T. Synlett 1992, 255-265. (e) Mikami, K.; Shimizu, M. Chem. Rev. 1992, 92, 1021-1050. (f) Yamamoto, H.; Maruoka, K.; Furuta, K. In Selectivities in Lewis Acid Promoted Reactions; Schinzer, D., Ed; Kluwer Academic Publishers: London, 1989; pp 281-294.
5. Reviews: (a) Mikami, K. Pure Appl. Chem. 1996, 68, 639-644. (b) Mikami, K. In Advances in Asymmetric Synthesis; Hassner, A., Ed.; JAI Press: Greenwich, Connecticut, 1995; Vol. 1, pp 1-44. (c) Mikami, K.; Terada, M.; Nakai, T. In Advances in Catalytic Processes; Doyle, M. P., Ed.; JAI Press: Greenwich, Connecticut, 1995; Vol. 1, pp 123-149. (d) Mikami, K.; Terada, M.; Narisawa, S.; Nakai , T. Synlett 1992, 255-265. (e) Mikami, K.; Shimizu, M. Chem. Rev. 1992, 92, 1021-1050. (f) Yamamoto, H.; Maruoka, K.; Furuta, K. In Selectivities in Lewis Acid Promoted Reactions; Schinzer, D., Ed; Kluwer Academic Publishers: London, 1989; pp 281-294.
6. Reviews: (a) Mikami, K. Pure Appl. Chem. 1996, 68, 639-644. (b) Mikami, K. In Advances in Asymmetric Synthesis; Hassner, A., Ed.; JAI Press: Greenwich, Connecticut, 1995; Vol. 1, pp 1-44. (c) Mikami, K.; Terada, M.; Nakai, T. In Advances in Catalytic Processes; Doyle, M. P., Ed.; JAI Press: Greenwich, Connecticut, 1995; Vol. 1, pp 123-149. (d) Mikami, K.; Terada, M.; Narisawa, S.; Nakai , T. Synlett 1992, 255-265. (e) Mikami, K.; Shimizu, M. Chem. Rev. 1992, 92, 1021-1050. (f) Yamamoto, H.; Maruoka, K.; Furuta, K. In Selectivities in Lewis Acid Promoted Reactions; Schinzer, D., Ed; Kluwer Academic Publishers: London, 1989; pp 281-294.
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8. Reviews on ene reactions: (a) Hoffmann, H. M. R. Angew. Chem., Int. Ed. Engl. 1969, 8, 556-577. (b) Fujita, Y.; Suzuki, S.; Kanehira, K. J. Synth. Org. Chem., Jpn. 1983, 41, 1152-1167. (c) Snider, B. B. In Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 2, pp 527-561 and Vol. 5, pp 1-27. (d) Oppolzer, W. Angew. Chem., Int. Ed. Engl. 1978, 17, 476-486.
9. Reviews on ene reactions: (a) Hoffmann, H. M. R. Angew. Chem., Int. Ed. Engl. 1969, 8, 556-577. (b) Fujita, Y.; Suzuki, S.; Kanehira, K. J. Synth. Org. Chem., Jpn. 1983, 41, 1152-1167. (c) Snider, B. B. In Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 2, pp 527-561 and Vol. 5, pp 1-27. (d) Oppolzer, W. Angew. Chem., Int. Ed. Engl. 1978, 17, 476-486.
10. Reviews on ene reactions: (a) Hoffmann, H. M. R. Angew. Chem., Int. Ed. Engl. 1969, 8, 556-577. (b) Fujita, Y.; Suzuki, S.; Kanehira, K. J. Synth. Org. Chem., Jpn. 1983, 41, 1152-1167. (c) Snider, B. B. In Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 2, pp 527-561 and Vol. 5, pp 1-27. (d) Oppolzer, W. Angew. Chem., Int. Ed. Engl. 1978, 17, 476-486.
11. Reviews on ene reactions: (a) Hoffmann, H. M. R. Angew. Chem., Int. Ed. Engl. 1969, 8, 556-577. (b) Fujita, Y.; Suzuki, S.; Kanehira, K. J. Synth. Org. Chem., Jpn. 1983, 41, 1152-1167. (c) Snider, B. B. In Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 2, pp 527-561 and Vol. 5, pp 1-27. (d) Oppolzer, W. Angew. Chem., Int. Ed. Engl. 1978, 17, 476-486.
12. Reviews: (a) Katsuki, T.; Martin, V. S. Org. React. 1996, 48, 1-299. (b) Johnson, R. A.; Sharpless, K. B. In Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 7, pp 389-436. (c) Finn, M. G.; Sharpless, K. B. In Asymmetric Synthesis, Morrison, J. D., Ed; Academic Press: New York, 1985; Vol. 5, pp 247-308. (d) Rossiter, B. E. In Asymmetric Synthesis, Morrison, J. D., Ed; Academic Press: New York, 1985; Vol. 5, pp 193-246.
13. Reviews: (a) Katsuki, T.; Martin, V. S. Org. React. 1996, 48, 1-299. (b) Johnson, R. A.; Sharpless, K. B. In Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 7, pp 389-436. (c) Finn, M. G.; Sharpless, K. B. In Asymmetric Synthesis, Morrison, J. D., Ed; Academic Press: New York, 1985; Vol. 5, pp 247-308. (d) Rossiter, B. E. In Asymmetric Synthesis, Morrison, J. D., Ed; Academic Press: New York, 1985; Vol. 5, pp 193-246.
14. Reviews: (a) Katsuki, T.; Martin, V. S. Org. React. 1996, 48, 1-299. (b) Johnson, R. A.; Sharpless, K. B. In Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 7, pp 389-436. (c) Finn, M. G.; Sharpless, K. B. In Asymmetric Synthesis, Morrison, J. D., Ed; Academic Press: New York, 1985; Vol. 5, pp 247-308. (d) Rossiter, B. E. In Asymmetric Synthesis, Morrison, J. D., Ed; Academic Press: New York, 1985; Vol. 5, pp 193-246.
15. Reviews: (a) Katsuki, T.; Martin, V. S. Org. React. 1996, 48, 1-299. (b) Johnson, R. A.; Sharpless, K. B. In Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 7, pp 389-436. (c) Finn, M. G.; Sharpless, K. B. In Asymmetric Synthesis, Morrison, J. D., Ed; Academic Press: New York, 1985; Vol. 5, pp 247-308. (d) Rossiter, B. E. In Asymmetric Synthesis, Morrison, J. D., Ed; Academic Press: New York, 1985; Vol. 5, pp 193-246.
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26. Glyoxylate-ene reaction with homoallylic ethers: (a) Mikami, K.; Shimizu, M.; Nakai, T. J. Org. Chem. 1991, 56, 2952-2953. (b) Mikami, K.; Yoshida, A. Tetrahedron Lett. 1994, 35, 7793-7796.
27. Glyoxylate-ene reaction with homoallylic ethers: (a) Mikami, K.; Shimizu, M.; Nakai, T. J. Org. Chem. 1991, 56, 2952-2953. (b) Mikami, K.; Yoshida, A. Tetrahedron Lett. 1994, 35, 7793-7796.
28. -1.
29. For the 6-membered transition state model for the Lewis acid-promoted carbonyl-ene reactions: Mikami, K.; Loh, T.-P.; Nakai, T. Tetrahedron Lett. 1988, 29, 6305-6308.
30. Sharpless asymmetric epoxidation of (E)-allylic alcohols has been reported to proceed with remarkably high level of enantioselectivity (>95% ee) (ref. 3).
31. 3) δ 172.4, 166.5, 137.1, 132.0, 129.8, 128.5, 128.4, 128.3, 128.1, 127.3, 123.2 (q, J = 287.4 Hz), 84.5, 75.23, 72.71, 65.38, 55.14, 54.25, 52.76, 52.03, 35.18.
32. Roush, W. R.; Brown, R. J.; DiMare, M. J. Org. Chem. 1983, 48, 5083-5093. Also see: Minami, N.; Ko, S. S.; Kishi, Y. J. Am. Chem. Soc. 1982, 104, 1109-1111.
33. Roush, W. R.; Brown, R. J.; DiMare, M. J. Org. Chem. 1983, 48, 5083-5093. Also see: Minami, N.; Ko, S. S.; Kishi, Y. J. Am. Chem. Soc. 1982, 104, 1109-1111.
34. 3).
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